(2S)-2''-(2'''-hydroxyisopropyl)-dihydrofurano[2'',3'':7,8]-4'-hydroxy-5-methoxyflavanone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2S)-2''-(2'''-hydroxyisopropyl)-dihydrofurano[2'',3'':7,8]-4'-hydroxy-5-methoxyflavanone
• 英文别名: (2S)-2"-(2'''-hydroxy-2'''-propyl)-dihydrofurano[2",3":7,8]-4'-hydroxy-5-methoxyflavanone；(2S)-4′-hydroxy-5-methoxy-2”-(1-hydroxy-1-methylethyl)dihydrofuro[2,3-h]flavanone；(2S)-2-(4-hydroxyphenyl)-8-(2-hydroxypropan-2-yl)-5-methoxy-2,3,8,9-tetrahydrofuro[2,3-h]chromen-4-one
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: FWTSPMKFNWEBKW-BUSXIPJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4',7-二羟基-5-甲氧基-8-(3-甲基-2-丁烯基)黄烷酮 在 Fusarium oxysporum f.sp. lini KCTC 16325 作用下， 生成 (2R)-4′-hydroxy-5-methoxy-2”-(1-hydroxy-1-methylethyl)dihydrofuro[2,3-h]flavanone 、 (2S)-2''-(2'''-hydroxyisopropyl)-dihydrofurano[2'',3'':7,8]-4'-hydroxy-5-methoxyflavanone
  参考文献：
  名称：

  蛇麻草异黄酮异黄腐酚的生物转化代谢产物。

  摘要：

  关于微生物的代谢转化研究是预测哺乳动物系统中有机化合物异种生物代谢的最有用工具之一。啤酒中的主要啤酒花异戊烯基黄酮异黄腐酚（1）的微生物生物转化已导致产生了三对非对映异构体的氧化代谢产物（2⁻7）。异戊二烯基的环氧化或羟基化形成1的微生物代谢产物，HPLC，NMR和CD分析表明，所有产物均为由（2S）-和（2R）-异构体组成的非对映异构对。这些代谢化合物的结构被阐明为（2S，2“ S）-和（2R，2” S）-4'-羟基-5-甲氧基-7,8-（2,2-二甲基-3-羟基-2,3-二氢-4H-吡喃基）-黄酮（2和3），（2S）-和（2R）-7,4'-二羟基-5-甲氧基-8-（2，

  DOI：

  10.3390/molecules24030394

文献信息

• Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro
  作者：Tomasz Tronina、Agnieszka Bartmańska、Beata Filip-Psurska、Joanna Wietrzyk、Jarosław Popłoński、Ewa Huszcza

  DOI：10.1016/j.bmc.2013.01.026

  日期：2013.4

  Xanthohumol (1) and xanthohumol D (2) were isolated from spent hops. Isoxanthohumol (3) was obtained from xanthohumol by isomerisation in alkaline solution. Six metabolites were obtained as a result of transformation of xanthohumol (1) by selected fungal cultures. Their structures were established on the basis of their spectral data. One of them: 2 ''-(2'''-hydroxyisopropyl)-dihydrofurano-[4 '',5 '':3',4']-4',2-dihydroxy-6'-methoxy-alpha,beta-dihydrochalcone (6) has not been previously reported in the literature. The antioxidant properties of hops flavonoids and xanthohumol derivatives were investigated using the 2,2'-diplienyl-1-picrylhydrazyl (DPPH) radical scavenging method. The effects of these compounds on proliferation of MCF-7, PC-3 and HT-29 human cancer cell lines were determined by the SRB assay. With the exception of one metabolite, all tested compounds showed antiproliferative activity against the tested human cancer lines. alpha,beta-Dihydroxanthohumol (4), obtained through the biotransformation of xanthohumol, showed higher antiproliferative activity against MCF-7 human breast carcinoma cell line than cisplatin, a widely used anticancer therapeutic agent, and a comparably high activity against PC-3 human prostate cancer cell line. (C) 2013 Elsevier Ltd. All rights reserved.
• Biotransformed Metabolites of the Hop Prenylflavanone Isoxanthohumol
  作者：Hyun Jung Kim、Soon-Ho Yim、Fubo Han、Bok Yun Kang、Hyun Jin Choi、Da-Woon Jung、Darren R. Williams、Kirk R. Gustafson、Edward J. Kennelly、Ik-Soo Lee

  DOI：10.3390/molecules24030394

  日期：——

  of (2S)- and (2R)- isomers. The structures of these metabolic compounds were elucidated to be (2S,2"S)- and (2R,2"S)-4'-hydroxy-5-methoxy-7,8-(2,2-dimethyl-3-hydroxy-2,3-dihydro-4H-pyrano)-flavanones (2 and 3), (2S)- and (2R)-7,4'-dihydroxy-5-methoxy-8-(2,3-dihydroxy-3-methylbutyl)-flavanones (4 and 5) which were new oxygenated derivatives, along with (2R)- and (2S)-4'-hydroxy-5-methoxy-2"-(1-hydr

  关于微生物的代谢转化研究是预测哺乳动物系统中有机化合物异种生物代谢的最有用工具之一。啤酒中的主要啤酒花异戊烯基黄酮异黄腐酚（1）的微生物生物转化已导致产生了三对非对映异构体的氧化代谢产物（2⁻7）。异戊二烯基的环氧化或羟基化形成1的微生物代谢产物，HPLC，NMR和CD分析表明，所有产物均为由（2S）-和（2R）-异构体组成的非对映异构对。这些代谢化合物的结构被阐明为（2S，2“ S）-和（2R，2” S）-4'-羟基-5-甲氧基-7,8-（2,2-二甲基-3-羟基-2,3-二氢-4H-吡喃基）-黄酮（2和3），（2S）-和（2R）-7,4'-二羟基-5-甲氧基-8-（2，